methyl 6,11-dihydro-12-hydroxy-2,6,11-trioxo-2H-naphtho[2,3-g]chromene-4-carboxylate | 1312024-60-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: methyl 6,11-dihydro-12-hydroxy-2,6,11-trioxo-2H-naphtho[2,3-g]chromene-4-carboxylate
• 英文别名: Methyl 6,11-dihydro-12-hydroxy-2,6,11-trioxo-2h-naphtho[2,3-g]chromene-4-carboxylate；methyl 12-hydroxy-2,6,11-trioxonaphtho[2,3-g]chromene-4-carboxylate
• CAS: 1312024-60-4
• 化学式: C₁₉H₁₀O₇
• 分子量: 350.284
• InChiKey: NCUHQZZXFPLQAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,2-二羟基蒽醌 、 丁炔二酸二甲酯 在 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以95%的产率得到methyl 6,11-dihydro-12-hydroxy-2,6,11-trioxo-2H-naphtho[2,3-g]chromene-4-carboxylate
  参考文献：
  名称：

  Synthesis of new functionalized alizarins from alizarin, acetylenic esters, and phosphorus nucleophiles

  摘要：

  The 1:1 intermediate generated by the addition of triphenylphosphine to dialkyl acetylenedicarboxylates is trapped by alizarin to produce alkyl 6,11-dihydro-12-hydroxy-2,6,11-trioxo-2H-naphtho[2,3-g]chromene-4-carboxylates in good yields. When ethyl propiolate was used, the reaction afforded ethyl 6,11-dihydro-6,11-dioxoanthra[1,2-d][1,3]-dioxole-2-acetate. The reaction of dialkyl acetylenedicarboxylates, alizarin, and trialkyl phosphites produced dialkyl 2-(dialkoxyphosphoryl)-3-(9,10-dihydro-1-hydroxy-9,10-dioxoanthracen-2-yloxy)succinates.

  DOI：

  10.1007/s00706-011-0489-3

文献信息

• Synthesis of new functionalized alizarins from alizarin, acetylenic esters, and phosphorus nucleophiles
  作者：Issa Yavari、Leila Azad、Tayebeh Sanaeishoar

  DOI：10.1007/s00706-011-0489-3

  日期：2011.6

  The 1:1 intermediate generated by the addition of triphenylphosphine to dialkyl acetylenedicarboxylates is trapped by alizarin to produce alkyl 6,11-dihydro-12-hydroxy-2,6,11-trioxo-2H-naphtho[2,3-g]chromene-4-carboxylates in good yields. When ethyl propiolate was used, the reaction afforded ethyl 6,11-dihydro-6,11-dioxoanthra[1,2-d][1,3]-dioxole-2-acetate. The reaction of dialkyl acetylenedicarboxylates, alizarin, and trialkyl phosphites produced dialkyl 2-(dialkoxyphosphoryl)-3-(9,10-dihydro-1-hydroxy-9,10-dioxoanthracen-2-yloxy)succinates.